2-alkoxy-5-disubstituted barbituric acids.



ensures 'enrnni FFICE.

MAX ENGELBIANN. F ELBILRFIELD. GERMANY, ASSIGNOR T0 FAIRBENFABRIKEN VCR-M. FRIEDR. BAYER it C0,, 01* ELBERFELIJ, GERMANY, A CORPORATION OF GERMANY.

Q-ALKOXY-li-DISUBSTITUTEI) I SAlR-BITURIO ACIDS.

No Drawing.

Patented se t; 1o, 1912.

To all whom it may concern:

it known that 1, MAX Enonmmnn,

- doctor of philosophy, chemist, citizen of the German Empire, residing at Elbcrteld, Germany, have invented new and useful lmprovements in Q-Alkoxy-o-Disubstituted Barbituric Acids, of which the following is a. specification.

My invention concerns the production of the hitherto unknown Q-alkoXy-barbiturio acids of the formula:

(R is an elkyl, R is alkyl, and R an eroinatic substituent e. g. -C H -'-CH C H which have proved to be valuable soporifics, an average close being from it to lgrain. The process for their production consists in treating the ethers of isouree of the formula: on un (H -n substituent e. g. elkyl or arslkyl) or their salts with disubstituted malonyl lmloids.

The new products are crystalline compounds being converted by treating them with acids into the 5-clialkyl or arylnlkyl barbituric acids.

in order to illustrate the'new process more fully the following example is given, the parts being by weights-U0 parts of the 'mcthylethcr of isourca hydrochlorid:

stirring'ilit) parts of caustic soda lye (27 per cent.) are poured to this solution nnt1l the mixture reacts alkaline. .Vhen the re action is complete the benzene is distilled off. The 2-methoxy-5-phenylethyl-berbituric acid separates in a White crystalline shape. it is after drying recrystallized from alcohol. It melts at 152? C. and is ratherslightly soluble in cold Water but easily soluble in alcohol. benzene and acids. By heating the ether with an acid a. g. HCl

itis converted into the 5-phenylethylbarbituric acid. For this purpose 100 parts of the other are heated with 200 parts of a 30 per cent. hydrochloric acid on the Water bath chloromethyl being disengaged... The 2- methoXy-5-cliethylbarbitlu'ic acid melts at 131 C.

Instead of the methylether other derivatives g. 'isoureaethyl-ether or isoureabenzyl-ether can also be used.

l. The herein described Q-elkoxy-barbituric acids having motit, probably the formula in which R alkyl, R:alkyl, and R=an aromatic substituent, being crystalline powders; being converted. into 5-clisubstitutcd barbituric acids by treatment with a hot acid; and being valuable soporifics, substantially as described.

2. The herein described 2-methoxy-5- phcnyl-ethyl-harbituric acid being a White crystalline powder melting at 152 C. diilicultly soluble in cold water, easily soluble in alcohol, benzene and acids; and being a valuable soporific. substantially as described. In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

MAX. ENGELMANN. [Ls] Witnesses:

HELEN NUFER, A. NUFER. 

